Cesium carbonate → HCID 59651937, compound

HRID 2042650Notes

Reaction equation

HRID 2042650 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH2:26][CH2:25][C:24](=[O:27])[NH:23][N:22]=3)=[C:17]([F:28])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24](=[O:27])[NH:23][N:22]=3)=[C:17]([F:28])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 59652050HCID 59652050, compound

Product 1

HCID 59651937HCID 59651937, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a 10 mL round bottom flask, 4-[3-fluoro-4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (525 mg, 1.34 mmol), and cesium carbonate (874 mg, 2.68 mmol), in dimethylsulfoxide (5 mL) was heated to 135° C. 3 h. The reaction was cooled and the slurry was partitioned between methylene chloride and water extracted three times, and then dried over MgSO4. Purification with silica gel chromatography eluting with methylene chloride/methanol (95:5) produced 500 mg (93%). Mp 117-119° C. MS m/z 390 (M+H).

Workup

  1. custom3 h
  2. temperatureThe reaction was cooled
  3. customthe slurry was partitioned between methylene chloride and water
  4. extractionextracted three times
  5. dry with materialdried over MgSO4
  6. customPurification with silica gel chromatography
  7. washeluting with methylene chloride/methanol (95:5)
  8. customproduced 500 mg (93%)

Sources & evidence

ORD record
ord-941e1f76c4084e5b84963f803c06cd18
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

Loading…